Multicomponent Crystal Formation of Dexibuprofen-Caffeine to Improve Solubility http://www.doi.org/10.26538/tjnpr/v7i10.2
Article Sidebar
Main Article Content
Abstract
Alteration of solid form via a multicomponent crystal formation can be a choice to improve the solubility of a poor solubility drug, such as dexibuprofen. The purpose of this research was to produce dexibuprofen-caffeine (DXI-CAF) multicomponent crystal and to evaluate its solubility and dissolution rate. Preliminary investigation to predict the multicomponent crystal formation was conducted by observing crystal morphology by polarization microscope and knowing phase solubility type of DXI in caffeine solution. Liquid-assisted grinding (LAG) method was used to produce DXI-CAF multicomponent crystal and ethanol was used to accelerate its formation. Powder X-ray diffractometer (PXRD) and differential scanning calorimeter (DSC) were utilized to analyze DXI-CAF multicomponent crystal formation. Evaluation of physicochemical properties was carried out by the solubility testing in water and pH 1.2, 4.5, and 6.8. The dissolution rate tests were also performed in the same pH. The DXI-CAF showed a different crystal morphology from pure DXI and CAF after crystallized in ethanol. Meanwhile, a BS type curve was obtained from the determination of phase solubility. The LAG product revealed a distinctive PXRD pattern and DSC thermogram that was different from pure DXI and CAF, thereby indicating DXI-CAF multicomponent crystal formation. The increase in solubility and dissolution rate was shown in the DXI-CAF multicomponent crystal in all pH. Succinctly, DXICAF multicomponent crystal can be prepared by the LAG method which shows the potential in enhancing solubility and dissolution rate of dexibuprofen.
Article Details
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
References
Shekhawat P, Pokharkar V. Understanding peroral absorption: Regulatory aspects and contemporary approaches to tackling solubility and permeability hurdles. Acta Pharm Sin B 2017;7(3):260–280.
Faizah AK, Kresnamurti A. Evaluation of antiinflammatory activity of marine omega-3 in rats. Indones J Pharm Clin Res 2020;2(2):1–5.
Tran P, Park JS. Formulation of solid dispersion to improve dissolution and oral bioavailability of poorly soluble dexibuprofen. Pharm Dev Technol 2021;26(4):422–430.
Choi Y, Min KA, Kim CK. Development and evaluation of dexibuprofen formulation with fast onset and prolonged effect. Drug Dev Ind Pharm 2019;45(6):895–904.
Khalid Q, Ahmad M, Minhas MU. Synthesis of β- cyclodextrin hydrogel nanoparticles for improving the solubility of dexibuprofen: characterization and toxicity evaluation. Drug Dev Ind Pharm 2017;43(11):1873–1884.
Amombo Noa FM, Jacobs A. Phenylacetic acid co-crystals with acridine, caffeine, isonicotinamide and nicotinamide: Crystal structures, thermal analysis, FTIR spectroscopy and Hirshfeld surface analysis. J Mol Struct 2017;1139:60–66.
Reggane M, Wiest J, Saedtler M, Harlacher C, Gutmann M, Zottnick SH, Piechon P, Dix I, Müller-Buschbaum K, Holzgrabe U, Meinel L, Galli B. Bioinspired co-crystals of Imatinib providing enhanced kinetic solubility. Eur J Pharm Biopharm 2018;128:290–299.
Nechipadappu SK, Tekuri V, Trivedi DR. Pharmaceutical Co-Crystal of Flufenamic Acid: Synthesis and Characterization of Two Novel Drug-Drug Co-Crystal. J Pharm Sci 2017;106(5):1384–1390.
Thakuria R, Sarma B. Drug‑drug and drug‑nutraceutical cocrystal/salt as alternative medicine for combination therapy: A crystal engineering approach. Crystals 2018;8(2):101.
Rosyidi D, Radiati LE, Qosimah D, Amri IA, Prasetyo D, Anisa AK. The potential of Lampung robusta green coffee (Coffea canephora) extract toward T cell activation in ISAbrown laying chickens. Trop J Nat Prod Res 2022;6(6):875–878.
Abosede OO, Gordon AT, Dembaremba TO, Lorentino CMA, Frota HF, Santos ALS, Hosten EC, Ogunlaja AS. Trimesic acid-theophylline and isopthalic acid-caffeine
cocrystals: Synthesis, characterization, solubility, molecular docking, and antimicrobial activity. Cryst Growth Des 2020;20(5):3510–3522.
Luo Y, Chen S, Zhou J, Chen J, Tian L, Gao W, Zhang Y, Ma A, Li L, Zhou Z. Luteolin cocrystals : Characterization, evaluation of solubility, oral bioavailability and theoretical
calculation. J Drug Deliv Sci Technol 2019;50:248–254.
Latif S, Abbas N, Hussain A, Arshad MS, Bukhari NI, Afzal H, Riffat S, Ahmad Z. Development of paracetamol-caffeine co-crystals to improve compressional, formulation and in vivo performance. Drug Dev Ind Pharm 2018;44(7):1099–1108.
Wang C, Tong Q, Hou X, Hu S, Fang J, Sun CC. Enhancing Bioavailability of Dihydromyricetin through Inhibiting Precipitation of Soluble Cocrystals by a Crystallization Inhibitor. 2016;
Bučar DK, Henry RF, Lou X, Duerst RW, MacGillivray LR, Zhang GGZ. Cocrystals of caffeine and hydroxybenzoic acids composed of multiple supramolecular heterosynthons: Screening via solution-mediated phase transformation and structural characterization. Cryst Growth Des 2009;9(4):1932–1943.
Mantri RV, Sanghvi R, Zhu H (Jim). Solubility of pharmaceutical solids. In: Qiu Y, Chen Y, Zhang GGZ, Yu L, Mantri R a. V, editors. Developing Solid Oral Dosage Forms: Pharmaceutical Theory And Practice. London: Academic Press, 2017; p. 3–22.
Alatas F, Ratih H, Kurnia H, Soewandhi SN. Solubility enhancement of clozapine through co-crystal formation with isonicotinamide. Indones J Pharm 2019;2(1):1–6.
Jindal A, Prashar M, Dureja J, Dhingra N, Chadha K, Karan M, Chadha R. Pharmaceutical cocrystals of famotidine: structural and biopharmaceutical evaluation. J Pharm Sci 2022;11(10):2788–2798.
Chaudari KR, Savjani JK, Savjani KT, Shah H. Improved pharmaceutical properties of ritonavir through cocrystallization approach with liquid-assisted grinding method. Drug Dev Ind Pharm 2022;47(10):1633–1642.
Ren S, Liu M, Hong C, Li G, Sun J. The effects of pH, surfactant, ion concentration, coformer, and molecular arrangement on the solubility behavior of myricetin cocrystals. Acta Pharm Sin B 2019;9(1):59–73.
Alatas F, Aprilliana M, Gozali D. The preparation and solubility of loratadine-fumaric acid binary mixture. Asian J Pharm Clin Res 2017;10(1):331–334.
Kulla H, Greiser S, Benemann S, Rademann K, Emmerling F. In situ investigation of a Self-Accelerated cocrystal formation by grinding pyrazinamide with oxalic acid. Molecules 2016;21(7):16–18.
Hossain Mithu MS, Ross SA, Hurt AP, Douroumis D. Effect of mechanochemical grinding conditions on the formation of pharmaceutical cocrystals and co-amorphous solid forms of ketoconazole – Dicarboxylic acid. J Drug Deliv Sci Technol 2021;63:102508.
Ying P, Yu J, Su W. Liquid-Assisted Grinding Mechanochemistry in the Synthesis of Pharmaceuticals. 2021;1246–1271.
Zhang J, Wang L, Wang D, Gong J, Li W, Wang J. Solubility of dexibuprofen in different solvents from (263.15 to 293.15) K. J Chem Eng Data 2011;56(3):671–673.
Kumar S, Nanda A. Pharmaceutical cocrystals : An overview. Indian J Pharm Sci 2017;79(6):858–871.
Wisudyaningsih B, Setyawan D, Siswandono. Cocrystallization of quercetin and isonicotinamide using solvent evaporation method. Trop J Pharm Res 2018;18(4):672–702.
Berry DJ, Steed JW. Pharmaceutical cocrystals, salts and multicomponent systems; intermolecular interactions and property based design. Adv Drug Deliv Rev 2017;117:3–24.